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A kind of zwitterionic amino polyfluorene derivative and its synthesis method and application

A technology of ionic amines and derivatives, applied in the field of zwitterionic amine-based polyfluorene derivatives and their synthesis, to achieve the effects of easy processing and film formation, optimization, pollution reduction, and good environmental adaptability

Active Publication Date: 2017-08-18
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, polymerization with Suzuki is rarely reported

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  • A kind of zwitterionic amino polyfluorene derivative and its synthesis method and application
  • A kind of zwitterionic amino polyfluorene derivative and its synthesis method and application
  • A kind of zwitterionic amino polyfluorene derivative and its synthesis method and application

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Embodiment 1

[0035] 1) Synthesis of 2,7-dibromo-9,9-bis(2-ethylmorpholine)fluorene (M1)

[0036] 2,7-Dibromofluorene (6.5g, 20mmol), 4-(2-chloroethyl)morpholine hydrochloride (11.2g, 60mmol) and potassium hydroxide (11.3g, 200mmol) were dissolved in 200mL THF , reacted at 80oC for 48h in an anhydrous and oxygen-free Ar environment. After the reaction, the solvent tetrahydrofuran was distilled under reduced pressure, and the product was first purified by column chromatography (silica gel, ethyl acetate: methanol = 10:1 as the eluent), and the milky white solid was recrystallized in petroleum ether, and finally 5 g of white crystals were obtained. , the yield was 45%.

[0037] 2) PFNO-B-FNO-SO 3

[0038] In a 50mL three-necked flask, M1 (550mg, 1mmol), 1.4-dibenboronic acid (169mg, 1mmol), tetraphenylpalladium phosphide (15mg, 0.01mmol), potassium carbonate (1.38g, 10mmol) were added to 10mL of toluene 5mL water mixture. The reaction system was refluxed for 48 h under the protection of ...

example 2

[0040] 1) Synthesis of 2,7-dibromo-9,9-bis(2-ethylmorpholine)fluorene (M1)

[0041] 2,7-Dibromofluorene (6.5g, 20mmol), 4-(2-chloroethyl)morpholine hydrochloride (11.2g, 60mmol) and potassium hydroxide (11.3g, 200mmol) were dissolved in 200mL THF , reacted at 80oC for 48h in an anhydrous and oxygen-free Ar environment. After the reaction, the solvent tetrahydrofuran was distilled under reduced pressure, and the product was first purified by column chromatography (silica gel, ethyl acetate: methanol = 10:1 as the eluent), and the milky white solid was recrystallized in petroleum ether, and finally 5 g of white crystals were obtained. , the yield was 45%.

[0042] 2) Synthesis of 2,7-dibromo-9,9-dioctylfluorene (M2)

[0043] Put 2,7-dibromofluorene (5g, 15.5mmol), tetrabutylammonium bromide (0.1g, 0.31mmol), and 200mL dimethyl sulfoxide in a three-necked flask under vigorous stirring to form a suspension, drop 50wt % sodium hydroxide aqueous solution 5mL, after reacting for 1...

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Abstract

The invention discloses a zwitterionic amino polyfluorene derivative and a synthesis method and application thereof. The preparation method comprises the following steps: heating morpholine hydrochloride and potassium hydroxide for reflux reaction under the protection of an inert gas, recrystallizing a crude reaction product to obtain ethyl morpholine substituted dibromofluorene monomer; in the presence of a palladium catalyst, starting from a cyclic compound monomer with two brominated ends to obtain a cyclic compound monomer with boric acid ester; reacting the ethyl morpholine substituted dibromofluorene monomer with the cyclic compound monomer with the boric acid ester under the protection of the inert gas, cooling, taking an oil layer to drip into a non-polar solvent to obtain precipitation to obtain a neutral conjugated polymer, and processing by sulfonating and post processing to obtain the zwitterionic amino polyfluorene derivative. The zwitterionic amino polyfluorene derivative can be processed by using an environmental protection solvent such as water, alcohol and the like for dissolving, greatly reduces the pollution to the environment of solar cells, has a regular planar structure, good thermal stability and good adaptability to environment, and is easy in film processing.

Description

technical field [0001] The invention belongs to the technical field of organic solar cell materials, and in particular relates to a zwitterionic amino polyfluorene derivative and a synthesis method and application thereof. Background technique [0002] In recent years, due to its unique advantages, organic solar cells have attracted widespread attention from all walks of life, and their energy conversion rate has been continuously improved. Impressive progress has been made, and the best energy conversion rate has reached more than 10%. The energy conversion rate of organic solar cells continues to increase. In order to further improve battery efficiency, it is considered to introduce an interface modification layer that plays a key role in preparing high-performance battery devices and improving battery stability. Compared with the commonly used method of optimizing the active layer material, the method of interface modification reduces the contact resistance, thereby simul...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/02H01L51/42H01L51/46
CPCY02E10/549
Inventor 刘治田刘菁李超
Owner WUHAN INSTITUTE OF TECHNOLOGY
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